At the D: All Things Digital conference Wednesday, Steve Jobs and Bill Gates appeared onstage together for the first time in 20 years. One of the topics they discussed was Apple's series of Mac Dude and Windows Dork commercials:

Here in the present, while discussing some recent Apple commercials in which an Apple hipster out-talks a nerdy Windows guy, it seemed almost as if Jobs and Gates were acting in starring roles in the same ads. Jobs, in his black turtleneck and jeans and stubbled beard, looked ready for a night on the town, while Gates, in his striped, button-down shirt and slacks and black shoes, looked ready to get down to business.

And when Jobs tried selling Gates on the appeal of the new Apple ads, Gates wasn't buying.

"Part of those commercials is not to be mean, but the guys like each other," Jobs said.

I think a lot more people love the Windows dork played by John Hodgman than just his mother.

I'd like to see The Ad Whisperers take on those commercials, because I think they're a huge misfire on Apple's part. The Mac hipster played by Justin Long is insufferably smug compared to his problem-plagued comic foil, who ends up looking like a well-intentioned underdog unruffled by adversity. He's like Charlie Brown, falling over and over for Lucy's promise to let him kick the football.

When I spot one of those commercials as I'm blipping through Tivo, I stop to see how Hodgman fares. Like ad critic Seth Stevenson in Slate, I'm completely rooting for him:

The ads pose a seemingly obvious question -- would you rather be the laid-back young dude or the portly old dweeb? -- but I found myself consistently giving the "wrong" answer: I'd much sooner associate myself with Hodgman than with Long.

Mac has always gotten the design and the interface down pat. They just know it. PC's efforts to emulate this, and its constant failing, and its self-satisfied arrogance about it being the most used platform in the world, all of that made it very easy to craft a character who, while he is a boob, and often concerned about how he comes off, at his core really feels bad for the Mac. Is really so delusional to believe he’s much cooler than the Mac. The whole reason they're standing in that white room is because he’s trying to help the Mac out.

I'm not seeing that at all. At a time when the "Wow is Now" campaign for Windows Vista is laying an egg and Gates' exit leaves the company with a huge hole in the evangelism department, Apple has put the most sympathetic face on Microsoft in years.

Nice analysis, Rogers. Before this campaign started I was beginning to consider Mac ownership; now I would sooner write with a sharp stick and a clay tablet than associate myself with the cult. Reading Hodgman's thoughts on the character makes me like him a little less, too.